Wolff is an author known for his short stories and memoirs. He was originally born in 1945 in Birmingham,, Alabama. After serving in the United States Army during the Vietnam War ear, Wolff received a Honours degree in English from Hertford College and an M.A. From Stanford. He currently still teaches at Standford in English and Creative writing.
Wolff's first collection of short stories, In the Garden of North American Martyrs, was met with critical acclaim. His 1984 novella The Barracks Thief was awarded the PEN/Faulkner Award for Fiction in 1985. His 1989 memoir This Boy's Life was later turned into a movie starring Robert De Niro and Leonardo DiCaprio. Old School was first published in 2003 and is based on Wolff's own experiences at a boarding school in the 1960's.